Round Two

Jaclyn Siu

English Business Education Entrepreneurship Self-Improvement Technology

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Episodes 10

Avg. Duration 42m

Activity Highly Active

Since Jul 2025

Latest Episode May 2026

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Schedule

Every 2 Weeks

Format

Episodic

Consistency

Hosting

feeds.captivate.fm

About This Podcast

Join Jaclyn Siu, 3x founder and advocate for embracing entrepreneurship’s toughest moments, for honest conversations about failing forward. Each episode pulls back the curtain on startup life—the good, the gut-wrenching, and the unspoken—to help founders everywhere reclaim their stories, reinvent their identities, and rediscover their power.

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Recent Episodes

S2E3 Killing What You Built to Save It

May 04, 2026 47m

In this episode, three-time founder and startup advocate Jaclyn Siu sits down with Andrew Bennett, a self-described "person number six" at Provide, now Head of Small Business at Fifth Third Bank. The…

S2E2 Teaching Class With Zero Qualifications

Dec 17, 2025 42m

In this podcast episode, three-time founder and startup advocate Jaclyn Siu sits down with Tim He, a founder whose journey defies every expectation and embraces every contradiction.Tim went from…

S2E1 The Phone Call That Ended My Startup

Dec 03, 2025 55m

Two shutdowns. Two completely different emotional realities. One founder who lived both.In this episode of Round Two, host Jaclyn Siu sits down with Helena Fogarty — co-founder of Backable and host…

S1E6 The Things Founders Don’t Say Out Loud: A Bonus Round Two Talk

Nov 20, 2025 11m Bonus

Before Season Two of Round Two begins, we’re revisiting an unfiltered conversation with host Jaclyn Siu and fellow founder Jason about the parts of entrepreneurship that don’t make the highlight…

S1E5 Why This VC Says Failure Is the Best Founder Education

Sep 16, 2025 30m

In this podcast episode, three-time founder and startup advocate Jaclyn Siu discusses resilience, risk, and reframing failure with Rockman Ha, Head of Network & Ecosystem at The General…

S1E4 When 5x Ad Costs Erase All Your Startup Wins

Sep 02, 2025 34m

In this podcast episode, three-time founder and startup advocate Jaclyn Siu discusses failure, pivots, and the human cost of resilience in startups with Dave Rosen, former CEO of Wimo Games.About Our…

S1E3 No Plan, No Problem? The Scrappy Startup Playbook That Actually Worked

Aug 19, 2025 46m

In this episode, three-time founder and startup advocate Jaclyn Siu sits down with Izayah “Zay” Powell, Founder & COO of VidCade, to unpack why the best entrepreneurs treat failure like data—not…

S1E2 I Racked Up $250K in Debt Chasing Vanity Growth!

Aug 05, 2025 45m

In this episode of Round Two: From Setback to Comeback, three-time founder and Starcycle CEO Jaclyn Siu sits down with Jason Patel, Founder & CEO of Open Forge AI and previously Founder of…

S1E1 I Applied to Y Combinator 7 Times. Then I Shut the Company Down.

Jul 11, 2025 34m Transcript

In this podcast episode, three-time founder and startup advocate Jaclyn Siu discusses resilience, reinvention, and redefining failure with Daniel Ahmadizadeh, founder and CEO of Time.About Our…

Round Two - Launching July 2025

Jul 09, 2025 0m Trailer

When one of my startups shut down, I couldn’t talk about it.I shrugged. I changed the subject. I avoided the story, even though that chapter shaped me more than any success ever did.I’ve learned that…